John Updike once noted that within American fiction "the slot between the fantastic and the drab seems too narrow". Well, my playground is an even narrower slot: the slot between the terrific and the truly great. I am looking for the Greatest American Novelist of the last 100 years and I have created a knockout tournament to find my winner.

Here are the results from the top half of the first round draw.

The tie of the round

When reading around literature one hopes to enhance the reading experience by getting a better grasp of the writer, their intentions and their oeuvre, without succumbing to any influence or building any trammelling structures of preconception. Unfortunately, on this occasion, I built a structure of trepidation – as most of the articles pertaining to Messrs Faulkner and Gaddis advertised their difficulty.

Jonathan Franzen's essay about Gaddis, entitled Mr Difficult, is a case in point. Franzen, a man with an eggier head than me, didn't finish JR:

"One night, I gave up in the middle of a four-page paragraph and for the next few nights I was out late. When I opened JR again I was lost. I set it aside, hoping to pick up the threads some other night. Two months later, I quietly reshelved it. The bookmark remained stuck on page 469, attesting to my defeat by JR or to JR's defeat by my noisy life."

Yikes! I thought, I have a noisy life – it's positively deafening.

It's a massive book, littered with obscure references, and is written almost entirely in unattributed speech, with no chapter breaks and very little paragraphing. So, I left it on my chest of drawers. The beautiful Dalkey Archive edition, a great monochrome monolith, haunted my bedroom like a baleful Groke. One day I ventured closer to the book I'd been avoiding for months, and upon opening I found this piloerecting dedication:

"For Matthew. Once more unto the breach, dear friend, once more."

That's me! My name's Matthew, he's talking to me! If he'd added "noblest English", I might really have thought it was written for me and not for his son. It girded my loins nevertheless, and I summoned up, not blood, but the Gaddis Annotations and dived in. The Gaddis Annotations is a wonderful resource that comprehensively explains the obscure references that underpin the book. Although it could be enjoyed without it, I feel it would be peevish, like refusing to dunk one's biscuit in a cup of tea.

JR is about the dangers of free-market enterprises running wild. If the financial system is left unchecked, it argues, and people focus only on profits, social, educational and artistic degradation are inevitable. First published more than 40 years ago, it stands as an unheeded prophecy of the financial turmoil in which the world now finds itself. At the centre of the novel is scruffy 11-year-old JR Vansant, who, on a school trip to Wall Street, becomes fascinated with stocks and shares and by applying some basic capitalist principles, turns a simple mail order enterprise into a financial conglomerate. He's motivated by childish greed and begins to believe he is something of a genius (even though he thinks the Jamaica, Queens subway stop is a Caribbean island and that Native American Indians live on a "preservation"). He is not immoral like the businessmen he is desperate to emulate, but amoral, like any prepubescent boy. He thinks greed is good because he doesn't know any better. Although he mostly stays within the letter of the law, he's very rarely within the spirit, and when it all collapses he wonders, "Why are they blaming me?" He feels as if he's part of the American dream – he wants to get ahead, and quickly – but he has little consideration for the ordinary Americans his machinations may affect.

JR requires dedication. This is a book best read in great chunks in great silence, sitting under a great, bright window. Within the multi-layered conversations and one-sided telephone calls is a deeply funny, shrewd novel, coloured by the palpable anger Gaddis felt over the seeming indifference with which his first novel, The Recognitions, was met. At one point in the book, a writer is asked if his novel is difficult. He replies: "'As difficult as I can make it.'" And this novel certainly is difficult, too. The length alone is off-putting and there are only so many sequestered Sundays to pore over it. So, inevitably, I lost the thread sometimes; I became bored and confused on more than one occasion and eventually this became a book that was sometimes endured rather than enjoyed, but always admired.

Faulkner is also synonymous with difficulty but I was encouraged by Sarah Churchwell's assessment of Absalom, Absalom! as Faulkner's crowning masterpiece and steeled by Faulkner's sound (and maybe furious) advice to those who claim not to understand his writing, even after they read it two or three times: "Read it four times."

This is the humour that pervades the book, not in subject matter but in the style; the tangential, logorrheic sentences whirl around one's head like bejewelled dancers, mocking and laughing, and we begin to see how Quentin feels. Quentin is the conduit; he's us and we're him. He is sitting at the knees of the multifarious storytellers and he takes turns at relaying the story too, to his Harvard roommate. The story troubles and bullies him. This is the bud of an arc to another of Faulkner's works – and who doesn't love an arc?

I followed Faulkner's advice and pored over the text, reading and re-reading and imbibing again. I'm not always taken by a modernist style but his is impressive and beautiful and buries the plot deep within itself.

The book is irrigated with colons, semi-colons and parentheses punctuating lengthy paragraphs, to the point where little faces appear, (perhaps Faulkner was the first purveyor of emoticons ;). I wouldn't put anything past him). The writing is mellifluous and intoxicating and depicts the thrilling story of the ruthless Thomas Sutpen and his determined Southern settlement. It takes us up to and through the Civil War and the rise and demise of Sutpen and his family. The story is brilliantly revealed through many overlapping accounts, tales told from different points of view in the Southern tradition like stories on the porch but all washed in the same, high-coloured prose. Only a poor settler, Wash Jones, is allowed to speak in his natural "yokel voice" and for him Faulkner reserves a special role.

It's a book that deals with race, slavery, incest, war, ambition and greed. It attacks the self-righteousness of the Southern aristocracy and left me soaked to the skin, sweaty with "the South". This was a difficult book that was still thoroughly enjoyable. It had to be fine to beat JR and this is certainly a great, great novel by an epicure of language.

Winner: Absalom, Absalom!

The Other Results

In That Old Ace in the Hole, Annie Proulx introduces us to a legion of idiosyncratic characters all with crazy names that combine to produce a pleasing but unspectacular plot. It's more a collection of short stories, a "marshalling of facts", than the flowing novel that her superlative style deserves.

Naked Lunch is a bare-back, drug-fuelled, violently sexual romp through dystopian urban settings. It's a work that defies classification but also defies understanding. It is occasionally humorous and visceral but mostly repetitive and confusing. It is an important novel that smashed apart the American censorship laws but I found reading Burroughs' letters and interviews far more pleasing and interesting than deciphering his art.

There is a fine line between genius and madness and in Burroughs's frenzied attempt to produce both he totally baffled this reader. So, whilst That Old Ace in the Hole is by no means "great", Proulx's style and dry, backwater wit win through.

Wharton's satire of early 20th-century marriage and a woman's role in the upper echelons of American and French society, is a piece of sheer aesthetic beauty. The plot unravels elegantly but the greatest delight is her unparalleled prose. Everything is so perfectly intoned, so brilliantly expressed; it is an utter joy to read.

"It was after the war that the struggles began." Joseph Heller switches from war to middle-class suburban misery. His jaundiced views of work and family life are so relatable and yet so terrifying: "I don't know how I got here and I don't know how I'm going to get out." This novel is a dark beast of desolate nostalgia but imbued with Heller's trademark sardonic humour and a gnawing and worrying truth.

It came down to the beautiful versus the beastly and as the man said, "Twas Beauty killed the Beast".

I was taken by the bitter beauty of both these novels; stories about love affairs that show how strange, delightful and dangerous love can be. Giovanni's Room is the story of David, a young American who sails to France to "find himself". He meets the intoxicating Giovanni and embarks on a troubled love affair. But when David's girlfriend returns to Paris, he is unable to admit the truth and his dishonesty results in tragedy.

A Farewell to Arms tells of a love affair between an injured American lieutenant and his nurse, set in the midst and confusion of the first world war. Dialogue, action, drama; Hemingway does them all with precision and power to produce a novel that lives long in the memory.

It was a close thing but Hemingway takes the day, not least for that devastating passage: "The world breaks everyone …"

Le Guin rises above the perceived limitations of her genre to produce a thought-provoking tale tinged with melancholy and wonder. George Orr has vivid dreams that can retroactively alter reality. His psychiatrist tries to harness these dreams to "make things better" with fascinating and destructive consequences. Le Guin creates many alternative realities with relish and aplomb and great style, but cannot avoid the inevitable inconsistencies that come when a writer dabbles with causality. Worse still are the inconsistencies of character and the occasionally clunky plot devices.

As Harry "Rabbit" Angstrom knows only too well, "after you've been first-rate at something, no matter what, it kind of takes the kick out of being second-rate". This is a first-rate novel with a second-rate subject: the American man's suburban malaise. It feels a little old-fashioned now, and perhaps Heller's Something Happened is a more original rendering of a man trapped in his own life. But, Updike has that special sheen, a filigree of wisdom and style so pleasing that it transcends its subject matter. I decided that I'd like to see where Rabbit will run to and so the winner by a (twitching) nose is Updike.

Billy Bathgate is resourceful, smart as a whip and has an ambition to become part of the famous Dutch Schultz gang. He is the perfect narrator, a quiet 15-year-old who lives by his bold instincts and for whom observing, evaluating and learning has become an occupation. Although he starts merely as a vessel for the story, he's drawn into the brutal, visceral, fascinating world of the gangsters.

Doctorow's achievement here is, for me, astonishing. His plot is so tight it allows him the freedom to create extreme beauty out of viciousness. There is eroticism without lasciviousness, nostalgia without sentimentality. Billy Bathgate is a packed novel that supplies immense pleasure.

Oates gives us a true family saga. The Mulvaneys are the American dream family until an ugly incident sends their lives spiralling out of their control. Oates's garrulous style builds true depth behind her characters so that we really care about their plight. It is entertaining and vivacious but just could not live with the brilliance of Billy Bathgate.

42nd Parallel and Libra are based around real events. The first shows the early part of the 20th century, up to the outbreak of the first world war, and the latter zooms in on the hinge of the American century: the assassination of John F Kennedy. Both writers use fiction to tickle the belly of history and produce novels of high art and enjoyment.

Dos Passos's novel, the first in his USA trilogy, is composed of four distinct components that together create an atmospheric and fragmented "chronicle" of the time. Dos Passos tells the stories of a few different characters and shows us how people lived and loved as the century grew. In order to locate his characters he adds other distinct sections: Newsreel, The Camera Eye and potted biographies of important figures that helped to sculpt the age. Dos Passos's writing is impressive but the real star here is Libra; a brilliant portrayal of Lee Harvey Oswald's life, around which he weaves a dark and creeping conspiracy. Such humour, wisdom, style and entertainment.

I fear that Auster was done for before a single page was turned. The Grapes of Wrath is rightly considered a masterpiece; a clarion call for proletarian America and an example of what people mean when they try to define the Great American Novel. Its flaws are well documented – clanging symbolism, an over-egging of the socialist pudding and accusations of sentimentality – but when a diamond is this big, you don't see the flaws. The Joads' dramatic exodus from the dust bowls of Oklahoma is written with great power and emotion. A wonderful novel.

I also really enjoyed The Book of Illusions. Auster is an irresistible storyteller and this novel fairly skipped along. It's a two-stranded novel of tragedy and the redemption one finds in love and artistic inspiration. The two threads meet in a thrilling and fraught conclusion. But it could not hold up against a true American classic.